Article
Biochemistry & Molecular Biology
Gita Matuleviciute, Egle Arbaciauskiene, Neringa Kleiziene, Vilija Kederiene, Greta Ragaite, Migle Dagiliene, Aurimas Bieliauskas, Vaida Milisiunaite, Frank A. Slok, Algirdas Sackus
Summary: A series of novel heterocyclic amino acid compounds were developed and regioselectively synthesized as N-Boc protected esters, serving as achiral and chiral building blocks. The structures of these compounds were confirmed through H-1, C-13, and N-15-NMR spectroscopy and HRMS investigation.
Article
Biochemistry & Molecular Biology
Mary C. C. Hennessy, Hirenkumar Gandhi, Timothy P. P. O'Sullivan
Summary: A methodology for synthesizing γ, δ-unsaturated β-keto esters through asymmetric peroxidation is described. The cinchona-derived organocatalyst allows for high enantioselectivity (up to 95:5) in obtaining the desired γ-peroxy-β-keto esters. Furthermore, the resulting δ-peroxy esters can be easily reduced to chiral δ-hydroxy-β-keto esters without affecting the functionality of the β-keto ester. Importantly, this chemistry provides a concise route to chiral 1,2-dioxolanes, a common motif in bioactive natural products, via a novel P2O5-mediated cyclization of the corresponding δ-peroxy-β-hydroxy esters.
Article
Chemistry, Organic
Kodipura P. Sukrutha, Toreshettahally R. Swaroop, Ramesh Preetham, Neratur K. Lokanath, Kanchugarakoppal S. Rangappa, Maralinganadoddi P. Sadashiva
Summary: The N-alkylation of amines by the reaction with xanthate esters in the presence of acetic acid catalyst in ethanol is efficient, environmentally friendly, and a general approach. A probable mechanism for the N-alkylation of amines is proposed in the study.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Multidisciplinary Sciences
Lin-Xin Ruan, Bo Sun, Jia-Ming Liu, Shi-Liang Shi
Summary: Despite the importance of enantioenriched tertiary alcohols bearing two contiguous stereocenters, their efficient synthesis has remained a challenge. In this study, we report a platform for their preparation using nickel-catalyzed addition of organoboronates to racemic ketones, achieving high levels of diastereo- and enantioselectivity.
Article
Chemistry, Organic
Swarnayu Banik, Tanmoy Sahoo, B. Sridhar, B. V. Subba Reddy
Summary: A chiral Cu(i)-bisoxazoline complex was used to catalyze the enantioselective electrophilic fluorination of 3-indolinone-2-carboxylates with NFSI, resulting in the production of chiral 2-fluoro-3-indolinone-2-carboxylates in good yields with excellent enantioselectivities. This marks the first report of enantioselective fluorination of 2-substituted 3-indolinones using a chiral Cu(i)-bisoxazoline complex.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xin Liu, Thomas Werner
Summary: A manganese pincer complex is reported as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes, leading to the corresponding alcohols, amines, and methanol. This method represents an approach to the indirect reduction of CO2 and shows the first examples of reduction of carbamates and urea derivatives as well as C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is demonstrated by successful reduction of various compounds with good to excellent yields.
Review
Chemistry, Organic
Christian D. -T. Nielsen, Joshua D. Linfoot, Alexander F. Williams, Alan C. Spivey
Summary: This review surveys recent synergistic applications of combining chiral organocatalysts with achiral metals for stereoselective transformations. The transformations are classified based on reactivity modes, focusing on organocatalytic activation of carbonyl substrates as chiral nucleophiles and electrophiles in combination with achiral metal co-catalysts. Radical reactions mediated by achiral metal complexes via photocatalysis are also presented, revealing privileged structures and highlighting opportunities for further development in this exciting field.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Shinnosuke Kitayama, Hiroaki Shimizu, Satoshi Yokoshima
Summary: In this study, photoirradiation of alpha-(2-nitrophenyl)ketones resulted in the production of cyclic hydroxamates. The reaction involved photoinduced oxygen transfer from the nitro group to the benzylic position, leading to the formation of an alpha-hydroxyketone with a nitroso group. Subsequent addition of the nitroso group to the ketone moiety and the cleavage of the C-C sigma bond between the carbonyl group and the benzyl position produced hydroxamic acid, which then underwent hemiacetal formation to yield cyclic hydroxamate.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Agricultural Engineering
Lin Dai, Wenfei Jiang, Runqian Jia, Xin Zhou, Yong Xu
Summary: This study developed an acetic acid-mediated bio-oxidation strategy with Gluconobacter oxydans to produce valuable 2-ketogluconic acid from lignocellulosic biomass. Acetic acid was found to have a down-regulated effect on biooxidizing glucose to gluconic acid while significantly facilitating 2-ketogluconic acid accumulation and improving gluconate dehydrogenase activity. These findings provide a theoretical foundation for the industrial production of 2-ketogluconic acid using lignocellulosic materials.
BIORESOURCE TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Weiyang Guan, Yejin Chang, Song Lin
Summary: We have developed a new, unified method for the conversion of benzylic and allylic alcohols, aldehydes, and ketones into boronic esters under electroreductive conditions. This approach utilizes readily available pinacolborane as both an activator and an electrophile, allowing for the generation of a redox-active trialkylborate species, which then delivers the desired deoxygenatively borylated products. This strategy can be applied to various substrates and is suitable for late-stage functionalization of complex molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Xianjun Xu, Huangdi Feng, Erik V. Van der Eycken
Summary: An efficient synthesis route for unsymmetric 1,4-diamino-2-butynes has been developed using a microwave-assisted Cu(I)-catalyzed cross-A(3)-coupling/decarboxylative coupling process. The multicomponent reaction yields target products in moderate to good yields with high chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jie Xu, Fangling Lu, Linghong Sun, Mingna Huang, Jianwei Jiang, Ke Wang, Dandan Ouyang, Lijun Lu, Aiwen Lei
Summary: The construction of C-S bonds plays a crucial role in synthetic, medicinal, and materials chemistry. In this study, we used an electrochemical reduction method to obtain thiyl radicals from sulfinic acids. This approach enabled the synthesis of a variety of desired thioesters in high yields. The preliminary mechanism studies revealed that the formation of thiyl radical species from sulfinic acid involved multiple steps of a single electron transfer process.
Review
Chemistry, Multidisciplinary
Philipp Spiess, Saad Shaaban, Daniel Kaiser, Nuno Maulide
Summary: Umpolung is a term describing the reversal of innate polarity, which has become an important tool in synthetic organic chemistry. In this Account, the authors provide an overview of established methods and summarize their findings in the rapidly developing field of umpolung of carbonyl derivatives. They focus on the alpha-umpolung of amides enabled by electrophilic activation and the enolonium chemistry of ketones enabled by hypervalent iodine reagents. The authors discuss the challenges and achievements of these reactions, as well as mechanistic aspects. Rating: 8/10.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Organic
Swetha Sathyendran, Kesavan Muthu, Karthick Govindan, Nian-Qi Chen, Wei-Yu Lin, Gopal Chandru Senadi
Summary: A FeCl3-catalyzed decyanation of alpha-aminonitriles followed by a [4 + 2] annulation with terminal alkynes has been developed for the synthesis of 2,4-diaryl quinolines. The reaction showed good tolerance towards various aniline, aldehyde, and arylacetylene derivatives, providing moderate to good yields of the desired products. Control experiments suggested a nonradical pathway involving Povarov-type [4 + 2] annulation from an in situ generated iminium species. The method demonstrated the capability for gram-scale synthesis, continuous-flow process, and successful application with styrene.
Article
Chemistry, Multidisciplinary
Bence S. Nagy, Gang Fu, Christopher A. Hone, C. Oliver Kappe, Sandor B. Oetvoes
Summary: A continuous in situ persulfuric acid generator was developed and applied for oxidative esterification of aldehydes under flow conditions. The method demonstrated good safety, sustainability, and scalability, making it significant for organic synthesis.
Article
Chemistry, Organic
Maryam Shokoohian, Nourallah Hazeri, Malek Taher Maghsoodlou, Mojtaba Lashkari
Summary: New 1,2,4-triazine derivatives, as biologically active heterocyclics, were synthesized in the presence of acetic acid as a result of the reaction of pyridine-2-(1H)-one derivatives with 1,2-dicarbonyl compounds at 50 degrees C, and their biological properties were also investigated.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Sadegh Talaiefar, Sayyed Mostafa Habibi-Khorassani, Mehdi Shaharaki
Summary: The full chemical kinetics of a four-component condensation reaction for the synthesis of pyranopyrazoles has been investigated spectrally. The reactions involving ethyl acetoacetate, hydrazine hydrate, malononitrile, and various substituents of benzaldehyde were studied. The reaction with para electron-withdrawing substituted benzaldehyde showed the largest negative Delta S-double dagger value. The unfavorable Delta S-double dagger value was compensated by a favorable Delta H-double dagger value. This correlated with a faster reaction rate and a lower Delta G-double dagger value. The study also revealed the importance of resonance and inductive effects in stabilizing the reaction center with a strong electron-withdrawing group.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Zahra Aelami, Malek Taher Maghsoodlou, Reza Heydari, Afshin Yazdani-Elah-Abadi
Summary: An efficient and novel synthetic protocol for constructing aminomethylene cycloalkane-1,3-diones based on anthraquinone scaffold has been developed. The green synthetic procedure involves amino-methylene bond formation and has been successful in a one-pot reaction at room temperature, yielding the desired products in good yields. The chemical structures of these compounds were identified using various analytical techniques, and their DNA binding activities were investigated using electronic absorption spectra UV-vis.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Sara Zhaleh, Nourallah Hazeri, Mohammad Reza Faghihi, Malek Taher Maghsoodlou
Summary: In this study, medicinally important amidoalkyl naphthoquinones were synthesized via an eco-friendly and straightforward method. The one-pot multicomponent reaction successfully prepared the precursors of these natural compounds, which are of great significance in medicinal research. The synthesized compounds were characterized using various techniques.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Mojtaba Lashkari, Farzaneh Mohamadpour, Malek Taher Maghsoodlou, Reza Heydari, Nourallah Hazeri
Summary: A naturally biodegradable, reusable, and eco-safe catalyst called uric acid has been developed for the green, facile and economical one-pot synthesis of pyran annulated heterocyclic systems. This study provides insight into the reliability of the catalyst in aiding the formation of heterocyclic compounds. The method offers high atom economy, cleaner reaction profile, simple column-free work up condition, shorter reaction times, high to excellent yields, eco-safety, and high catalytic activity, making it an interesting alternative to multistep approaches.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Energy & Fuels
Marzieh Cheraghipoor, Davod Mohebbi-Kalhori, Meissam Noroozifar, Malek Taher Maghsoodlou
Summary: In this study, ceramic membranes with different compositions were fabricated and used as separators in microbial fuel cells (MFCs). The addition of SiO2 to the membrane had varying effects on MFCs performance, with significant improvements observed when 30% SiO2 was added to non-leached soil.
Article
Chemistry, Organic
Samanehsadat Sharifi, Malek Taher Maghsoudlou, Nourallah Hazeri
Summary: This research utilized a green process to synthesize chromen derivatives using a one-pot reaction in water at a low temperature with the catalytic effect of KF/Clinoptilolite nanoparticles. The procedure has advantages such as short reaction time, excellent yield, and the ability to use various substrates.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Multidisciplinary
Homayoun Faroughi Niya, Nourallah Hazeri, Malek Taher Maghsoodlou, Maryam Fatahpour
Summary: This research successfully synthesized a novel acidic nanocatalyst for the efficient synthesis of 2-amino-3-cyanopyridine derivatives. The nanocatalyst offers advantages such as simplicity of work-up, high stability, and environmental friendliness.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Physical
Homayoun Faroughi Niya, Nourallah Hazeri, Maryam Fatahpour, Parvin Roudini, Moheb Shirzaei
Summary: This study presents a new approach for developing nanomaterials, specifically Fe3O4@THAM-Pd MNPs as a nanocatalyst. The structure was confirmed using various techniques and the catalytic efficiency and stability were demonstrated in the synthesis of bis (pyrazolyl)methane derivatives. The strong interaction between N-rich shells and Pd nanoparticles contributes to the stability of the nanocatalyst.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Mahboobeh Rezaie Kahkhaie, Nourallah Hazeri, Malek Taher Maghsoodlou, Afshin Yazdani-Elah-Abadi
Summary: The study introduces a novel nanocatalyst for the synthesis of biologically important compounds, demonstrating efficient catalytic performance and easy recovery for multiple reuse.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Physical
Ghasem Marandi, Reyhaneh Nadernia, Nourallah Hazeri, Malek Taher Maghsoodlou
Summary: The synthesis of 3,4-dihydropyrano[2,3-c]chromene and pyrano[2,3-d]pyrimidine derivatives using vitamin B-12 as a catalyst in a one-pot reaction of malononitrile, benzaldehydes, and 4-hydroxycumarine or 1,3-dimethylbarbituric acid is reported and has gained attention in recent years.
IRANIAN JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Organic
Fatemeh Noori Sadeh, Mojtaba Lashkari, Nourallah Hazeri, Maryam Fatahpour, Malek Taher Maghsoodlou, Mohammad Saeed Hadavi, Sahar Mahnaei
Summary: A series of biologically varied compounds were synthesized using an eco-friendly catalyst under mild conditions, with high yields, short reaction times, and environmental friendliness. The catalyst showed high stability during the reaction and could be reused multiple times without loss of performance.
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Dilek Isik Tasgin, Irem Bayraktar
Summary: We present a synthetic method for pyrrolizine-3-one derivatives and investigate their photophysical properties. These compounds are prepared through a series of reactions involving substituted pyrroles in one-pot, two-step oxidation, and intramolecular cyclization processes. The photophysical properties of the synthesized compounds are studied using UV-Vis and fluorescence spectroscopy in various solvents. The introduction of pyrrolyl substituents has a significant impact on Stokes shifts and quantum yield values.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Satish Kumar Burra, Vaikunta Rao Lakinani, Raghunadh Akula, Chiranjeevi Yankkanti
Summary: A novel and green strategy for the construction of biologically relevant substituted indolyl-4H-chromenes scaffolds is reported, using L-proline as a catalyst and water as a promoter solvent. This catalytic system offers wider applicability, shorter reaction times, and high yields, making it an ideal condition for green chemistry.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Abouelhaoul El Alami, Amine El Maraghi, Fatima Youssoufi, Assiya Atif, Hamid Sdassi
Summary: Nitrobenzimidazoles have become increasingly important in the design of new compounds in medicinal, therapeutic and chemical fields. This review provides an overview of the synthesis strategies and biological activities of nitrobenzimidazole derivatives.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Nilesh Raghunath Khedkar, Alex Joseph, Milind Sindkhedkar
Summary: In this study, a new library of 3-(2-(pyrimidin-5-yl)thiazol-4-yl)-1,2,4-oxadiazole compounds was designed and synthesized as potential anticancer agents using in silico fragment-based drug design. The compounds were tested for their anticancer activity in vitro, and one compound exhibited excellent activity against multiple cancer cell lines.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Terungwa H. Iorkula, Bryce A. Tolman, Scott R. Burt, Matt A. Peterson
Summary: A new method for synthesizing C-6 substituted products has been discovered in this study, which utilizes lower doses of fluoride and CsF as a catalyst, with high reaction yields and cost-effectiveness under suitable conditions.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Ranjana Aggarwal, Swati Sharma
Summary: This review article mainly focuses on the synthesis of 3(5)-trifluoromethylpyrazoles via condensation reaction of trifluoromethyl-beta-diketones with hydrazines. It emphasizes the importance of fluorine-containing compounds and pyrazoles in the field of biology. The literature reported condensation reactions of trifluoromethyl-beta-diketones with hydrazines are covered.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
F. M. Alshareef, Sami A. Al-Harbi, Esam S. Allehyani, Omeima Abdullah, Magdy A. Ibrahim
Summary: This study aimed to construct a novel category of linear annulated chromeno[3',2':5,6]pyrido[2,3-d][1,3]thiazolo[3,2-a]pyrimidines. The chemical reactivity of the synthesized compounds was investigated, and they showed significant antimicrobial activity against various strains.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Preethi Dhanapal, S. L. Manju
Summary: Thiazole based Schiff base scaffolds have become an integral part of drug development in recent years, playing a versatile role as building blocks for lead drug molecules. This study presents a facile one pot synthetic method for producing novel 4-aryl thiazoles with high yield, shorter reaction time, and milder conditions, without the need for catalysts or purification techniques.
SYNTHETIC COMMUNICATIONS
(2024)
